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2005
Pyridine derivatives
R 0380
Synthesis and Solid-State Structures of Alkyl-Substituted 3-Cyano-2-pyridones.
Closely related cyanopyridones (III), (V), and (VIII) are prepared following three
08- 146 —
routes; (III) is synthesized by a literature method, this compound is converted to (V) by
a deprotonation step using in situ generated LDA and the subsequent alkylation of the
dianionic intermediate. The synthesis of (VIII) is based on the condensation and
cyclization of (II) with intermediary 1,3-dicarbonyl compounds, which are prepared in
situ by a base-catalyzed formylation of ketones (VI). Two different supramolecular
structures are observed in the solid state: the formation of symmetric dimers of the
R22 (8) type or the helical chains of the C(4) type. The solid-state structures can be
divided in two groups. The first one is characterized through little external influence
on the hydrogen bonding array while the second one is characterized through a larger
external influence. — (FISCHER, C. B.; POLBORN, K.; STEININGER, H.; ZIPSE,
H.; Z. Naturforsch., B: Chem. Sci. 59 (2004) 10, 1121-1131; Fachbereich Chem.,
Ludwig-Maximilians-Univ., D-81377 Muenchen, Germany; Eng.) —
H. Hoennerscheid